Methods of Preparation of Carboxylic Acids, Acidity in Carboxylic Acids, Benzoin Condensation, Benzil-Benzilic Acid Rearrangement is considered one of the most asked concept.
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Carboxylic acids have higher boiling points than aldehydes, ketones and even alcohols of comparable molecular mass. It is due to their:

more extensive association of carboxylic acid via van der Waals force of attraction

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formation of carboxylate ion

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formation of intramolecular H-bonding

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formation of intermolecular H-bonding

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Which of the following statements about the depletion of the ozone layer is correct?

The problem of ozone depletion is less serious at poles because NO₂ solidifies and is not available for consuming ClO^• radicals.

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The problem of ozone depletion is more serious at poles because ice crystals in the clouds over poles act as catalyst for photochemical reactions involving the decomposition of ozone by Cl^•and ClO^• radicals.

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Freons, chlorofluorocarbons, are inert chemically, they do not react with ozone in stratosphere.

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Oxides of nitrogen also do not react with ozone in stratosphere.

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Major product of the following reaction is :

CH₃COOH +

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HCOOH +

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CH₃CHO +

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HCHO +

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$\mathrm{CH}_3-\mathrm{CH}(\mathrm{OH}) \mathrm{CH}_3+\mathrm{Br}_2 \xrightarrow{\mathrm{Na}_2 \mathrm{CO}_3 / \Delta} \mathrm{CH}_3-\mathrm{CO} \overline{\mathrm{O}} \mathrm{Na}^{+}+(\mathrm{P})$

product (P) is

$\mathrm{CHBr}_3$

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$\mathrm{CH}_3-\mathrm{Br}$

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$\mathrm{CH}_4$

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$\mathrm{CH}_3-\mathrm{CH}_3$

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The aldehydes which will NOT form Grignard product with one equivalent Grignard reagents are :

(B), (D)

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(B), (C),(D)

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(B), (C)

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(C), (D)

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In the following sequence of reactions $\mathrm{CH}_3-\mathrm{Br} \xrightarrow{\mathrm{KCN}} \mathrm{A} \xrightarrow{\mathrm{H}_3 \mathrm{O}^{+}} \mathrm{B} \xrightarrow[\text { ether }]{\mathrm{LiAlH}_4} \mathrm{C}$, the end product (C) is:

Acetone

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Methane

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Acetaldehyde

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Ethyl alcohol

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Which dicarboxylic acid in presence of a dehydrating agent is least reactive to give an anhydride ?

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In a set of reactions, ethyl benzene yielded a product D.

'D' would be :

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Consider the following equilibrium

$\mathrm{AgCl} \downarrow+2 \mathrm{NH}_3 \rightleftharpoons\left[\mathrm{Ag}\left(\mathrm{NH}_3\right)_2\right]^{+}+\mathrm{Cl}^{-}$

White precipitate of AgCl appears on adding which of the following ?

$\mathrm{NH}_3$

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aqueous NaCl

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aqueous $\mathrm{HNO}_3$

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aqueous $\mathrm{NH}_4 \mathrm{Cl}$

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Consider the coordination compound, [Co(NH₃)₆]Cl₃.

In the formation of this complex, the species which acts as the Lewis acid is :

$\left [ Co\left ( NH_{3} \right )_{6} \right ]^{3+}$

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$Cl^{-}$

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$Co^{3+}$

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$NH_{3}$

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Concepts Covered - 6

Methods of Preparation of Carboxylic Acids

From Esters
Esters on acidic hydrolysis give acids, while on basic hydrolysis give carboxylates, which on acidification give corresponding acids. The reaction occurs as follows:

From Grignard reagents
Grignard reagents with dry ice forms salts of carboxylic acids which after acidification give corresponding carboxylic acids. The reaction occurs as follows:

From Nitriles and Amides
Nitriles are hydrolysed in acidic or basic medium first to amides and then to acids. The reaction occurs as follows:

Chemical Properties of Carboxylic Acids

Formation of Anhydride
Carboxylic acid on heating with H₂SO₄ or P₂O₅ gives corresponding anhydride. The reaction occurs as follows:

Reaction with Ammonia
On heating with NH₃, carboxylic acid gives ammonium salt which on further heating at high temperature gives amides. The reaction occurs as follows:

Reduction
Carboxylic acids are reduced to 1^o alcohol by LiALH₄ or better with B₂H₆. B₂H₆ does not easily reduce esters, nitro, and halo groups, and NaBH₄ does not reduce (-COOH) group. The reaction occurs as follows:

Decarboxylation
When sodium salts of carboxylic acids are heated with soda lime (NaOH and CaO in 3:1 ratio), they form hydrocarbons by losing CO₂. This is known as decarboxylation. The reaction occurs as follows:

Kolbe's electrolysis
The electrolysis of aqueous solution of sodium or potassium salts of carboxylic acid makes the carboxylic acid to undergo decarboxylation to form alkane. The reaction occurs as follows:

Halogenation
The method of preparing α-chloro or α-bromo acid is by Hell-Volhard-Zelinsky reaction, which is carried out by treating the acid with Cl₂ or Br₂ in the presence of a small amount of red phosphorous. The reaction occurs as follows:

Ring substitution
Aromatic carboxylic acid undergoes substitution electrophilic reactions in which the (-COOH) group acts as a deactivating and meta-directing group. It does not undergo Friedel-Crafts reaction because the (-COOH) group is deactivating and the catalyst AlCl₃ gets bonded to the (COOH) group. The reactions occur as follows:

Acidity in Carboxylic Acids

Carboxylic acids are weaker than mineral acids but they are stronger than alcohols, phenols and peroxy acids.

Phenols are stronger acids than alcohols.
Carboxylic acids are stronger acids than phenols.
Carboxylic acids are stronger than peroxy acids.
Formic acid is stronger is a stronger acid than benzoic acid.

Perkin's Condensation

Aromatic aldehydes when heated with the anhydride of an aliphatic acid (containing two $\alpha$ -H atoms) in the presence of its sodium or potassium salt result in condensation to form α,β-unsaturated acid.

Mechanism

For example,

Reformatsky Reaction

Ketones and aldehydes react with α-bromoesters(BrCHRCOOEt) and Zn in benzene to form β-hydroxy esters. First the zinc organometallic BrZnCHRCOOEt is formed and then it adds to the (C=O).

Mechanism

For example,

Benzoin Condensation, Benzil-Benzilic Acid Rearrangement

Benzoin condensation
When benzaldehyde is refluxed with aq. alcoholic KCN solution to give benzoin( $\alpha$ -hydroxy ketone), the process is called benzoin condensation.

Mechanism